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WO2003020859A2 - Procede de durcissement de matieres grasses insaturees - Google Patents

Procede de durcissement de matieres grasses insaturees Download PDF

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Publication number
WO2003020859A2
WO2003020859A2 PCT/EP2002/009321 EP0209321W WO03020859A2 WO 2003020859 A2 WO2003020859 A2 WO 2003020859A2 EP 0209321 W EP0209321 W EP 0209321W WO 03020859 A2 WO03020859 A2 WO 03020859A2
Authority
WO
WIPO (PCT)
Prior art keywords
unsaturated
fatty substances
unsaturated carboxylic
unsaturated fatty
carboxylic acid
Prior art date
Application number
PCT/EP2002/009321
Other languages
German (de)
English (en)
Other versions
WO2003020859A3 (fr
Inventor
Gerrit Pelzer
Lars Zander
Ulrich Ruigk
Lothar Friesenhagen
Bernhard Gutsche
Norbert Klein
Ingomar Mrozek
Egbert Gritz
Horst Josten
Wilhelm Kuhr
Original Assignee
Cognis Deutschland Gmbh & Co. Kg
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cognis Deutschland Gmbh & Co. Kg filed Critical Cognis Deutschland Gmbh & Co. Kg
Priority to JP2003525117A priority Critical patent/JP2005501907A/ja
Priority to EP02797601A priority patent/EP1432781A2/fr
Priority to US10/488,306 priority patent/US20040236127A1/en
Publication of WO2003020859A2 publication Critical patent/WO2003020859A2/fr
Publication of WO2003020859A3 publication Critical patent/WO2003020859A3/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/12—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation
    • C11C3/123—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation using catalysts based principally on nickel or derivates
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11B—PRODUCING, e.g. BY PRESSING RAW MATERIALS OR BY EXTRACTION FROM WASTE MATERIALS, REFINING OR PRESERVING FATS, FATTY SUBSTANCES, e.g. LANOLIN, FATTY OILS OR WAXES; ESSENTIAL OILS; PERFUMES
    • C11B15/00—Solidifying fatty oils, fats, or waxes by physical processes
    • C—CHEMISTRY; METALLURGY
    • C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
    • C11C—FATTY ACIDS FROM FATS, OILS OR WAXES; CANDLES; FATS, OILS OR FATTY ACIDS BY CHEMICAL MODIFICATION OF FATS, OILS, OR FATTY ACIDS OBTAINED THEREFROM
    • C11C3/00—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom
    • C11C3/12—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation
    • C11C3/126—Fats, oils, or fatty acids by chemical modification of fats, oils, or fatty acids obtained therefrom by hydrogenation using catalysts based principally on other metals or derivates

Definitions

  • the invention is in the field of oleochemical raw materials and relates to a new industrial process for curing unsaturated compounds.
  • Oleochemical raw materials from the natural fats and oils to the first finishing products, the fatty acids, fatty acid esters and fatty alcohols, are mixtures of unsaturated and saturated homologues, the degree of unsaturation essentially being due to the raw material used and the so-called iodine number is expressed.
  • synthetic substances that are obtained by fermentation of suitable paraffins are also currently gaining a role.
  • Long-chain dicarboxylic acids which are produced by biooxidation of paraffins or monocarboxylic acids in the presence of Candida tropicalis may be mentioned [cf. EP 0229252 AI (Henkel)].
  • the object of the present invention was to provide an improved process for hardening unsaturated fatty substances, especially unsaturated carboxylic acids and in particular unsaturated dicarboxylic acids, with the aid of which iodine numbers are below 2, preferably below 1 and in particular below 0 , 5 can be achieved, the reaction speed being simultaneously increased significantly compared to the known prior art.
  • the invention relates to a process for curing unsaturated fatty substances in the presence of transition metal catalysts, which is characterized in that the double bonds are saturated at pressures in the range from 100 to 300, preferably 150 to 280 and in particular 200 to 250 bar.
  • unsaturated fatty substances that serve as starting materials for hardening is not critical in itself.
  • Unsaturated carboxylic acids, unsaturated carboxylic acid alkyl esters and unsaturated carboxylic acid polyol esters are typically suitable for this purpose.
  • the unsaturated carboxylic acids preferably follow the formula (I)
  • a 1 represents a mono- or polyunsaturated, linear or branched hydrocarbon radical having 5 to 21 carbon atoms and R 1 represents hydrogen or a carboxyl group, ie it can be both mono- and dicarboxylic acids, the latter in this respect are preferred when the effect of increasing the reaction rate is most clearly shown there.
  • suitable monocarboxylic acids are the fatty acids having 6 to 22 and preferably 16 to 22 carbon atoms, such as palmoleic acid, oleic acid, elaidic acid, petroselinic acid, linoleic acid, linolenic acid, gadolinic acid and behenic acid and their technical mixtures.
  • branched unsaturated fatty acids which are obtained as a monomer fraction in the dimerization of unsaturated monocarboxylic acids, especially oleic acid.
  • Suitable dicarboxylic acids are those which have 3 to 22 carbon atoms, such as maleic acid and fumaric acid, and in particular those unsaturated dicarboxylic acids which are obtained by enzymatic carboxylation of the corresponding paraffins.
  • the unsaturated C 8 -dicarboxylic acid should be mentioned here in particular.
  • Such branched, optionally naphthenic di- and tricarboxylic acids can also be used as starting materials which are obtained in the oligomerization of unsaturated monocarboxylic acids and are usually referred to as dimer or trimer fatty acids.
  • carboxylic acids their alkyl esters can also be used.
  • the unsaturated carboxylic acid alkyl esters preferably follow the formula (II)
  • these are the ethyl, propyl, butyl, caprylic and preferably methyl esters of the abovementioned mono- and dicarboxylic acids.
  • the polyol esters, especially the glycerol esters can also be used instead of the alkyl esters.
  • Unsaturated carboxylic acid polyol esters are preferably unsaturated mono-, di- and / or triglycerides, which are usually natural oils with more or less high levels of unsaturated homologues in the mixture.
  • Typical examples are palm oil, palm kernel oil, coconut oil and beef tallow and preferably olive oil, sunflower oil, rapeseed oil, linseed oil, rice husk oil and the like.
  • Typical for the unsaturated fatty substances used is an iodine number in the range from 10 to 300, preferably 50 to 200 and in particular 70 to 125, which is reduced to values below 2, preferably below 1 and in particular below 0.5.
  • the unsaturated fatty substances can be present in a mixture with their saturated homologs, as long as the iodine number of the mixture is at least 10.
  • transition metals are suitable as hardening catalysts, among which nickel and in particular palladium are particularly preferred. These metals are preferably present on supports, silicon dioxide and, in particular, activated carbon being particularly suitable for this purpose.
  • Pd / activated carbon catalysts as described, for example, in EP 0632747 B1 (Henkel), has proven to be particularly advantageous. With regard to the production and use of such catalysts, reference is made in full to the content of this document.
  • the unsaturated fatty substances can be hardened in a manner known per se, for example by arranging the catalyst in a fixed bed and bringing the reactant and hydrogen into contact with one another in a cocurrent or countercurrent process.
  • the temperatures for curing are usually in the range from 150 or 220 and preferably 180 or 200 ° C.
  • the process can of course also be carried out discontinuously, a continuous procedure is preferred, since in this way a sealed hydrogen cycle gas can be worked and the separate expansion and compression is eliminated.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Fats And Perfumes (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

L'invention concerne un procédé de durcissement de matières grasses insaturées en présence de catalyseurs de type métaux de transition. Ce procédé est caractérisé en ce que la saturation des liaisons doubles s'effectue à des pressions comprises entre 100 et 300 bars.
PCT/EP2002/009321 2001-08-30 2002-08-21 Procede de durcissement de matieres grasses insaturees WO2003020859A2 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2003525117A JP2005501907A (ja) 2001-08-30 2002-08-21 不飽和脂肪物の硬化方法
EP02797601A EP1432781A2 (fr) 2001-08-30 2002-08-21 Procede de durcissement de matieres grasses insaturees
US10/488,306 US20040236127A1 (en) 2001-08-30 2002-08-21 Method for hardening unsaturated fatty substances

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE10142306.3 2001-08-30
DE10142306A DE10142306A1 (de) 2001-08-30 2001-08-30 Verfahren zur Härtung von ungesättigten Fettstoffen

Publications (2)

Publication Number Publication Date
WO2003020859A2 true WO2003020859A2 (fr) 2003-03-13
WO2003020859A3 WO2003020859A3 (fr) 2003-09-18

Family

ID=7696982

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2002/009321 WO2003020859A2 (fr) 2001-08-30 2002-08-21 Procede de durcissement de matieres grasses insaturees

Country Status (5)

Country Link
US (1) US20040236127A1 (fr)
EP (1) EP1432781A2 (fr)
JP (1) JP2005501907A (fr)
DE (1) DE10142306A1 (fr)
WO (1) WO2003020859A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006504802A (ja) * 2002-10-29 2006-02-09 コグニス コーポレーション 醗酵培養液からのカルボン酸の単離

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ITMI20050723A1 (it) * 2005-04-21 2006-10-22 Consiglio Nazionale Ricerche Metodo di produzione del biodiesel
DE102007027371A1 (de) * 2007-06-11 2008-12-18 Cognis Oleochemicals Gmbh Verfahren zur Herstellung einer Verbindung aufweisend mindestens eine Ester-Gruppe
DE102008002092A1 (de) * 2008-05-30 2009-12-03 Evonik Degussa Gmbh Verfahren zur Herstellung von Dodeca-2, 10-dien-1, 12-dicarbonsäure bzw. 1, 12-Dodecandicarbonsäure mittels Ring-öffnender Kreuzmetathese (ROCM) von Cycloocten mit Acrylsäure
DE102008002090A1 (de) * 2008-05-30 2009-12-03 Evonik Degussa Gmbh Ungesättigte Dicarbonsäuren aus ungesättigten cyclischen Kohlenwasserstoffen und Acrylsäure mittels Metathese, deren Verwendung als Monomere für Polyamide, Polyester, Polyurethane sowie weitere Umsetzung zu DIolen und Diaminen
EP2371937A1 (fr) * 2010-03-26 2011-10-05 BASF Corporation Procédé pour l'hydrogénation d'acides gras en utilisant un catalyseur de nickel à promoteur

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB757484A (en) * 1951-10-05 1956-09-19 Nora Vittorio De Improved method and apparatus for the reduction of fatty materials by hydrogenation
GB1179504A (en) * 1966-04-07 1970-01-28 Unilever Ltd Hydrogenation of Unsaturated Aliphatic Compounds in Acid and Ester Solvents
EP0632747A1 (fr) * 1992-03-26 1995-01-11 Henkel Kgaa Catalyseur en coquille, son procede de production et son utilisation.
WO1996001304A1 (fr) * 1994-07-01 1996-01-18 Poul Möller Ledelses- Og Ingeniörrrådgivning Aps Procede d'hydrogenation d'un substrat et produits fabriques selon ce procede
DE19707579A1 (de) * 1997-02-26 1998-08-27 Bayer Ag Verfahren zur Hydrierung ungesättigter Fettsäureester
US5962711A (en) * 1994-07-01 1999-10-05 Poul Moller Ledelses- Og Ingeniorradgivning Aps Hydrogenation of substrate and products manufactured according to the process
US6194624B1 (en) * 1998-12-09 2001-02-27 Basf Aktiengesellschaft Hydrogenation of polyenes to monoenes

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE3602525A1 (de) * 1986-01-29 1987-07-30 Henkel Kgaa Verfahren zur kontinuierlichen heterogenkatalytischen hydrierung von fetten, fettsaeuren und fettsaeurederivaten

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB757484A (en) * 1951-10-05 1956-09-19 Nora Vittorio De Improved method and apparatus for the reduction of fatty materials by hydrogenation
GB1179504A (en) * 1966-04-07 1970-01-28 Unilever Ltd Hydrogenation of Unsaturated Aliphatic Compounds in Acid and Ester Solvents
EP0632747A1 (fr) * 1992-03-26 1995-01-11 Henkel Kgaa Catalyseur en coquille, son procede de production et son utilisation.
WO1996001304A1 (fr) * 1994-07-01 1996-01-18 Poul Möller Ledelses- Og Ingeniörrrådgivning Aps Procede d'hydrogenation d'un substrat et produits fabriques selon ce procede
US5962711A (en) * 1994-07-01 1999-10-05 Poul Moller Ledelses- Og Ingeniorradgivning Aps Hydrogenation of substrate and products manufactured according to the process
DE19707579A1 (de) * 1997-02-26 1998-08-27 Bayer Ag Verfahren zur Hydrierung ungesättigter Fettsäureester
US6194624B1 (en) * 1998-12-09 2001-02-27 Basf Aktiengesellschaft Hydrogenation of polyenes to monoenes

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2006504802A (ja) * 2002-10-29 2006-02-09 コグニス コーポレーション 醗酵培養液からのカルボン酸の単離

Also Published As

Publication number Publication date
EP1432781A2 (fr) 2004-06-30
WO2003020859A3 (fr) 2003-09-18
US20040236127A1 (en) 2004-11-25
DE10142306A1 (de) 2003-03-27
JP2005501907A (ja) 2005-01-20

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